If anybody could link me to any great RE books, podcasts or how or where I should start, just basically starting, then growing.

I purchased a whole bunch of real estate books to learn all the basics so I can engage intelligently in real estate related conversations and plan to join a local meetup group today. 

First off real estate is not a "job" but more of a career .you are an independent contractor, basically self employed, What you put into it you get out of it, you do not draw a wage or a salary , you are paid a commission, you get paid when a property closes. lets say you sell a property for 300,000 and the commission is 18,000.

But so you can answer let put down some basics.   

Rent larger home, use cash to rent a smaller home/move to retirement community (disadvantage: less community of older folks; advantage is we can continue to own the home but make money off of the rent payments; but now we have to manage new renters)Basically asking if anyone has experience moving to a retirement community, and what the optimal move is with our current real estate assets.Where could we talk to similar people in this situation?

Workforce class C housing in NYC ranges from $50k -$200k+/door.Not sure what type of capital you have, patient or fund equity... however a lot of owners in NYC are basically buying the dirt and/or are buying as legacy assets and capitalize on the appreciation. 

Construction cost will run between $100-250 per sq-ft depending on how basic (or nice) the design and whether you act as general contractor.

Take some classes at home depot or Loews on basic home maintenance, like fixing toilets and faucets and outlets and such, to save money on repairs. 

I've been trying to woo my wife for years.

@Chris Habets, I was living in the home and basically had a roommate who lived in the basement.